VS     

There are two programs that computer users feel very strongly about: 
their email client and their Web browser.

Computer users very rarely change any of these applications, and it takes
more than features to overcome the inertia and sense of comfort that you have
acquired after spending so many hours on either of these tools.  And even
though the Web browser has a very low retention threshold (except for your
bookmarks and your habits, you are not putting much at risk by switching
browsers), it’s quite interesting to see how many people are still using the
very first Web browser they started using.

The email client is even harder to switch away from, because the amount of
personal email that you have accumulated over the years is not just huge, it’s
also extremely personal.  Of course, there is also the added damage
that your email address might change in the process, forcing all your friends to
update their contact information for you.

With that in mind, it’s not without a certain sense of excitement that I
recently made the decision to switch away from Outlook to… 
GMail.

First of all, let me get something out of the way:  since I work for
Google, you might think my decision has a corporate side to it, but those of you
who read my weblog regularly know that I am fairly pragmatic person when it
comes to picking the most productive tools.  A year ago, I wrote a
comprehensive
comparison between Outlook 2003 and Thunderbird where I explained my
decision to prefer one over the other.

I spent these past months using both Outlook and GMail in an effort to
evaluate and compare these two tools.  Outlook sets the bar pretty high in
terms of functionalities and convenience, but what eventually tilted the scale
was my one-week vacation Hawaii last week.  More about this below.

Most of the Outlook pros and cons that I listed in the article above are
still completely valid (I can’t find one that no longer applies, actually), so I
guess that one interpretation of my switch is the realization that the drawbacks
of Outlook have finally reached a point where I no longer want to tolerate them,
and also because GMail has slowly gained functionalities that I considered
essential.  Overall, I still think that Outlook is more functional than
GMail, but given the rapid pace at which GMail is evolving and the diminishing
tolerance that I have for delays in my email reading, it still emerges as a
winner.

There are basically three factors that eventually broke the deal for Outlook: 
connectivity, spam handling and synchronization.

Connectivity

As I stated in the article above, Outlook is much more powerful and seamless
to use with an Exchange server than with IMAP.  The IMAP support doesn’t
seem to have received any kind of improvement these past years (not really
surprising) and not only does it lock up the interface very regularly, it’s also
extremely slow.  In contrast, GMail is always lightning fast, even on
slower lines (I regularly use in over my GPRS cell phone and the delays are
barely noticeable).

Spam handling

There are many anti-spam programs available for Outlook (I reviewed some of
them here) and
after a few evaluations, I had settled on SpamBully for Outlook, which is very
good but also very slow.  As a consequence, running it on an Inbox that
hasn’t been updated for a week can take almost an hour.  Yes, it’s that
slow.  But it was so good that I didn’t mind taking the hit.  GMail’s
spam filter has been absolutely terrific so far.

Synchronization

I access both my personal and work emails from a lot of different places: 
work desktops, work laptop, home desktop, home laptop and sometimes even, from
computers that I don’t own.  This latter option is obviously not possible
if you use Outlook as your main client, but even the first four types of
accesses are problematic.  So far, I was dodging the issue by using Remote
Desktop to log into my work machine, where my main Outlook client is always
running.  While Remote Desktop is an outstanding piece of software, this
technique has some serious limitations, mostly because of its
bandwidth-intensive nature.

Finally, there is one thing that has always been very clunky with Outlook and
to which I had somehow gotten used to (or rather, resigned myself to):  the
address book.  Despite many efforts, I have never really understood why
Outlook has so many places where it stores contact information (the Address
Book, Contacts and the online cache for completion).  I have never been
able to reconcile them or use them in a consistent manner.  As a result,
not only were my contacts scattered left and right in all these places, it was
also maddeningly difficult to create groups of email addresses (and also keep
them in sync as I make changes to the individual email addresses).

Now, there is one added benefit that completed my conversion to GMail: 
transparency.

In case you are not aware, you can start using GMail right now and you don’t
have to ask any of your friends to update their contact information for you if
you don’t want to.  This made possible by a critical GMail feature: "From
masking". You can tell GMail to display all the
emails you send from GMail as coming from another email address.  This
is really what makes everything work so well, and it’s a feature that was
recently added.  To configure your From address, go to Settings /
Accounts / Send Mail as.

Let’s see if GMail keeps its promises (and if you are curious to try it
yourself, email me and I’ll send you an invitation).